


Yes, Sir.

by benedictcumberlongpond



Category: Supernatural
Genre: AU, Business AU, Dirty Talk, Elevator Sex, Gift Fic, M/M, Office Sex, Spanking, Sub!Sammy, dom!Gabriel
Language: English
Status: Completed
Published: 2013-09-22
Updated: 2013-09-22
Packaged: 2017-12-27 06:51:24
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,226
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/975755
Author URL: https://archiveofourown.org/users/benedictcumberlongpond/pseuds/benedictcumberlongpond
Summary: <blockquote class="userstuff">
              <p>Gabriel is the CEO of his company, and he won't stand for his Personal Assistant acting like a little slut in the meeting room. Isaqueer Anniversary Fanfiction! Love those crazy, crazy ladies. Enjoy the porn.</p>
            </blockquote>





	Yes, Sir.

**Author's Note:**

  * For [Isaisanisa](https://archiveofourown.org/users/Isaisanisa/gifts).



Bluetooth headsets were for douche bags. 

Gabriel knew that. 

Sam had told him the first time he had seen Gabriel with one in his ear. 

Sam was the only one of his staff who could get away with shit like that without being fired, so Gabriel had just rolled his eyes and gestured to the tiny piece of machinery and muttered, 

“I’m relying on douche bags like me to buy these in order to maintain my company, okay Winchester?” and Sam had rolled his eyes, because he knew it wasn’t true. 

Gabriel didn’t really need the headsets at all, he made enough money from his phone company to keep him in the top ten wealthiest with his other three brothers. 

He owned the communications branch of his father’s company which had four sectors being run by him and his brothers respectively. 

Lucifer was on the Elite-Sports range, all shit about being ‘better than human’ with his cocky-ass expression plastered over the side of buildings, advertising sportswear and energy drinks and fucking god knows.

Michael was more secretive – often left out of press releases. Dealing with weaponry and having close contact with government agencies. When Gabriel had told Sam that, Sam had made some kind of joke about keeping him on the Christmas card list. 

Raphael worked in medicine and vaccinations, the brother with the most degrees (well, publicly anyway. No one knew how many degrees Michael had.) 

And their father? Lofty and absent, hadn’t been to a board meeting in years since he appointed his sons as CEO’s. 

That was fine for Gabriel. Let him go live it up, the old man was rich enough for retirement and Gabriel didn’t resent him for that. 

They were in a meeting as such today, all four of them around a huge table with their PA’s standing dutifully behind them like stone gargoyles. 

Lilith had been with Lucifer since he started, same as Michael and Rachel. Virgil was relatively new for Raphael, and Sam had only been with Gabriel a year. 

Sam was his favorite personal assistant. 

He had shuffled into the room, all flicky-hair and broad-shoulders and suit-and-tie with a Stanford degree and a smile like the sun and God, if Gabriel wasn’t so emotionally unequipped, he might have called it love. 

If asked, though, he would name it ‘tolerance’. 

Gabriel tolerated Sam, just like he tolerated his brothers who were all sitting pretentiously upright in their seats, except Lucifer. 

Lucifer was staring at something behind Gabe with his pen in his mouth, twirling it and flicking his tongue over the cap obscenely. 

Gabriel turned, trying to see what poor thing had caught Lucifer’s attention, when he realized it was Sam. 

Sam who was blushing and trying to keep his eyes down, who was returning Lucifer’s smirk with a shy smile. 

Now Gabriel wasn’t jealous of his brother, and he didn’t feel any ownership of Sam, but something in that moment made him feel like his whole brain had just tensed and untensed, and when he slammed a folder down on the table harder than necessary, successfully bringing Lucifer’s eyes back to the bench, the thrill of victory was for an entirely different reason than Sam no longer having eye contact with his older, taller, blonde, stubble-cheeked, smiling, _fucking_ brother. 

At the end of the meeting he stormed out of the room, muttering a harsh “Hurry up, Sam.” As he took off at a jog towards the elevator. 

“Keen to get out?” Sam asked jokingly, and Gabriel’s lips hardened because Sam should have been keen to get out but he probably wasn’t because he was too busy eye-fucking his older brother. 

The elevator chimed open and they both stepped inside, awkwardly silent in the small space. 

“Are you ok, Gabriel?” Sam asked in a small voice, and Gabriel could see his concerned reflection in the mirrors of the elevator. 

“How do you think I am, Sam? After seeing my personal assistant acting like a little slut in the meeting room?” Gabriel asked calmly, turning in the elevator and pressing the emergency stop button so the whole structure jolted to a halt. 

“I-I’m sorry, Gabriel.” Sam told him, falling to his knees and pressing his face into Gabriel’s hip. 

“I know you are, pet, but little sluts who act out have to get punished, don’t they?” Gabriel asked soothingly, pressing his fingers through Sam’s hair, untangling knots. 

“Yes, sir.” Sam said in a small voice

“Good boy, now how about you pull down your pants like a good whore and bend over for me?” Gabriel said, and Sam nodded, standing up and undoing the belt on his suit pants, pulling them down and then turning in the elevator, bracing his elbows against one of the bars near a mirror, watching Gabriel in the reflection. 

“What should we count to, Sam?” Gabriel asked pleasantly, walking over to where Sam was, rubbing a gentle hand over the delicious swell of his ass. 

“Twenty, sir?” Sam asked, pushing his ass out to get more contact, his eyelids fluttering, Gabriel could see his expression in the mirror. 

“Only twenty? You think you deserve that?” Gabriel asked, bringing his hand down suddenly to slap against Sam’s ass, the reverberating noise ringing in the small space. 

“Twenty five?” Sam asked hopefully, forehead pressing against the mirror now. 

“Hm,” Gabriel hummed, hand coming down again to slap in the same place, reddening the skin. 

“How many is that, Sam?” Gabriel asked as his hand rung over his ass again, and Sam gasped before replying. 

“Three, sir.” He managed 

“Yes, twenty-five should suffice.” Gabriel sighed as he raised his hand again. “Count nice and loud for me, Sammy.” 

\--

The people in reception said nothing as Gabriel Milton and his PA stepped through the building and towards the waiting limousine on the street. Not when they noticed the disarray of his PA’s hair, or the fact he was half-limping as he walked, or that there were drying tears smeared on his face and his lips were swollen and red. 

“Good boy,” Gabriel whispered under his breath as Sam held the door open for him, sliding into the car afterwards, bracketing him against the leather seats. 

“Good boys get rewards,” Sam reminded him, kissing Gabriel’s neck, fingers playing over his boss’ tie. 

“They do, don’t they?” Gabriel mused. “How about when we get back to HQ, you go ahead of me and make sure my desk is nice and tidy?” 

“Yes sir,” Sam breathed, sitting back in his seat and swallowing heavily. 

Gabriel had taught Sam different codes early in their sexual relationship, and he felt a thrill of excitement knowing that Sam was aware of what he expected, that Gabriel was going to walk into his office to find Sam, naked, spread out over his desk with his tight little hole facing outwards and his toes spread on the expensive carpet. 

Gabriel was hard already, almost impatient enough to pull Sam over by the hair and ask him to just suck his cock while they were waiting in the car. 

But no, he would wait. 

When they got to the office, though, Sam was nearly running to the elevator, and Gabriel gave him a head start, letting Sam get ready in his office. 

Eventually he made his way up as well, taking the time by himself in the elevator to take deep breaths, steady himself, adjust his rigid cock that was tenting the material of his trousers. 

The elevator dinged as it reached the top floor, and Gabriel walked out slowly, opening the door to his office and glancing inside. 

Sam was completely naked, his face pressed into the wood of Gabriel’s desk and his ass on display, little hole twitching now that Sam knew Gabriel was watching him. 

“Good boy,” Gabriel purred. “What would you like as a reward, Sammy?” 

“Y-your cock, sir.” Sam said, shivering as Gabriel’s footsteps echoed towards him, clicking across the floor as he came towards Sam and rubbed a hand against his ass, still cherry red from his spanking. 

“In here, baby?” Gabriel asked, fingers tapping against his rim carefully. 

“Please,” Sam breathed, pushing back. 

“Get me the lube, Sam.” Gabriel ordered, walking around his desk and sitting down in his chair, pulling open his laptop and opening his emails. 

Sam walked over to a cabinet on the other side of the room, pulling open a drawer to grab the lube and a condom. 

He walked back over to where Gabriel was, offering the lube and condom to him. 

“Pull out my cock,” Gabriel said off handedly, opening his first email and letting his eyes scan over the words. Sam put the condom and lube on the table and inched closer to Gabe, fingers slipping over his belt and touching his erection briefly before tugging down the zip and popping the button, pulling out Gabriel’s cock and letting it lay, thick and heavy against the expensive material. 

“Prep yourself, Sammy.” Gabriel said next, deleting the email after a curt reply. 

He heard the snick of the lube opening, then a moment of silence as Sam coated his fingers. There was a short groan as Sam slipped in his first finger, and Gabriel kept his eyes resolutely on the computer in front of him. 

“Ready yet?” Gabriel asked impatiently, letting his eyes meet Sam’s. He was leaning against Gabriel’s desk, one elbow braced as his other hand worked behind him, and Gabriel felt his cock twitch at the sight. 

“Almost,” Sam sighed, mouth gaping, face flushed. 

“Good,” Gabriel said, touching his own cock as he watched Sam worked, feeling the slick of precum against the silky head. 

“I-I think I’m ready n-now, sir.” Sam stuttered, and Gabriel knew his long fingertips were brushing against his prostate. 

“Good, put my condom on.” Gabriel told him, sitting back in his seat and spreading his thighs. Sam nodded and picked up the condom, tearing it open carefully and then rolling it over Gabriel’s cock, brushing delicate fingers over him. 

Gabriel watched him work and then nodded towards the desk. 

Sam caught his meaning, bending over the desk, bracing himself on the paperwork he had organized himself earlier that day, ass pushing backwards. 

Gabriel stood up from his seat, stepping close to Sam and rubbing the tip of his cock through the crack of his ass. 

“Please,” Sam moaned, and Gabriel pressed towards his personal assistant’s rim, letting the head of his cock begin to push in. 

Sam rolled his hips backwards, taking more of Gabriel’s cock in, and Gabriel hissed as his hands gripped Sam’s hips. 

“Stay still,” He ordered through clenched teeth, pressing in slowly until his cock was buried in that sweet ass and the material of his pants were pressed against Sam’s thighs. 

“Now ride me, Sam. And don’t crease the pants.” 

“Yes, sir.” Sam replied, thrusting forward towards the desk before pushing back, setting himself a punishing rhythm, and Gabriel could see his knuckles whitening against the edge of the desk. 

Gabriel bit his lip against the groans, letting himself help Sam, thrusting forwards on each backwards thrust, and soon Sam was crying out gently as his prostate was rubbed on each thrust. 

“Good boy, Sammy. Gonna come?” Gabriel asked pleasantly, fingers flexing against Sam’s hips.

“Can I touch myself?” Sam asked in response, and Gabriel slapped the cheek of his ass, 

“Can I touch myself, sir?” Sam corrected himself, and Gabriel smiled.

“Go on,” he permitted, and watched as Sam’s long fingers curled around his cock and gave it a few tugs, hand stuttering a slow rhythm that didn’t match the pace Gabriel was now slamming into him, cock pulling almost all the way out before pushing back in, fingers leaving marks on his hips, pressing over the fading ones with ferocity. 

Sam cried out as he came across Gabriel’s desk, a mixture of Gabriel’s name and a garbled prayer, his fingers slowing on his cock, his tight ass clenching around Gabriel’s cock. 

“Sam, fuck,” Gabriel managed as he thrusted in a few more times before coming, emptying into the condom. 

Sam slumped against the desk as Gabriel pulled out of him, taking off the condom and throwing it into the trash. He tucked himself back into his pants and tugged up the zipper.

“You need a glass of water, sweetie?” Gabriel asked playfully, kissing the base of Sam’s spine. 

“Yes please,” Sam responded, falling back into Gabriel’s chair and groaning. “And some ice for my ass,”

“Oh come on, it wasn’t that bad.” Gabriel pouted, and Sam smiled. 

“Love you,” he muttered, looking down at the desk. 

“Love you too, Sam.” Gabriel told him, walking over to the water cooler in his room, pulling down a plastic cup and filling it. “When’s my next meeting?” 

“Four,” Sam answered, standing up to locate his pants. “But you’ve got a phone call expected in… any minute now.” 

“Awesome. You coming back for lunch?” 

“Of course,” Sam answered, pulling on his pants and accepting the water from Gabriel, downing it on two gulps and pressing a kiss to Gabriel’s cheek. “Thanks Gabe,” 

Gabriel nodded as his blue tooth head set beeped, and Gabriel smiled as he put it on, answering the call with a smooth press of a few buttons. 

Sam still mouthed the word ‘douche bag’ as he pulled on his shirt.

**Author's Note:**

> Thanks for reading!


End file.
